• Bulletin of the Korean Chemical Society
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• v.28 no.9
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• pp.1519-1522
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• 2007

A new oleanane-type triterpenoid estersaponin, bodinierin C (1), along with two known saponins, mazusaponin I (2) and ciwujianoside C (3), were isolated from the water-soluble part of the root barks of Elsholtzia bodinieri. The structure of bodinierin C was characterized by spectroscopic means and chemical hydrolysis as 3β -Ocaffeoyl- 23-hydroxylechinocystic acid 28-O-α -L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-β- D-glucopyranosyl ester. The known compounds were identified by comparing their spectral data with those of authentic samples or data reported in the literature. All compounds were firstly isolated from Elsholtzia bodinieri family.

• Journal of Ginseng Research
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• v.36 no.1
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• pp.1-15
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• 2012

The major commercial ginsengs are Panax ginseng Meyer (Korean ginseng), P. quinquifolium L. (American ginseng), and P. notoginseng (Burk.) FH Chen (Notoginseng). P. ginseng is the most commonly used as an adaptogenic agent and has been shown to enhance physical performance, promote vitality, increase resistance to stress and aging, and have immunomodulatory activity. These ginsengs contain saponins, which can be classified as dammarane-type, ocotillol-type and oleanane-type oligoglycosides, and polysaccharides as main constituents. Dammarane ginsenosides are transformed into compounds such as the ginsenosides $Rg_3$, $Rg_5$, and $Rk_1$ by steaming and heating and are metabolized into metabolites such as compound K, ginsenoside $Rh_1$, proto- and panaxatriol by intestinal microflora. These metabolites are nonpolar, pharmacologically active and easily absorbed from the gastrointestinal tract. However, the activities metabolizing these constituents into bioactive compounds differ significantly among individuals because all individuals possess characteristic indigenous strains of intestinal bacteria. To overcome this difference, ginsengs fermented with enzymes or microbes have been developed.

• Proceedings of the Plant Resources Society of Korea Conference
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• 2012.05a
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• pp.20-20
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• 2012

Isoprenoids represent the most diverse group of metabolites, which are functionally and structurally identified in plant organism to date. Ginsenosides, glycosylated triterpenes, are considered to be the major pharmaceutically active ingredient of ginseng. Its backbones, categorized as protopanaxadiol (PPD), protopanaxatriol (PPT), and oleanane saponin, are synthesized via the isoprenoid pathway by cyclization of 2,3-oxidosqualene mediated with dammarenediol synthase or beta-amyrin synthase. The rate-limiting 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMGR), which is the first committed step enzyme catalyzes the cytoplasmic mevalonate (MVA) pathway for isoprenoid biosynthesis. DXP reductoisomerese (DXR), yields 2-C-methyl-D-erythritol 4-phosphate (MEP), is partly involved in isoprenoid biosynthesis via plastid. Squalene synthase and squalene epoxidase are involved right before the cyclization step. The triterpene backbone then undergoes various modifications, such as oxidation, substitution, and glycosylation. Here we will discuss general biosynthesis pathway for the production of ginsenoside and its modification based on their subcellular biological functions.

• Archives of Pharmacal Research
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• v.25 no.3
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• pp.270-274
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• 2002

Chromatographic separation of the stem bark extract of Mitragyna stipulosa afforded triterpene derivatives ursolic acid (1), quinovic acid (2), quinivic acid $3-O-{\beta}-D-glucopyranoside$ (3, quinovin glycoside C), quinovic acid 3-O-[$(2-O-sulfo)-{\beta}-D-quinovopyranoside$] (4, zygophyloside D) and quinovic acid $3-O-{\beta}-D-quinovopyranosyl-27-O-{\beta}-D-glucopyranosyl$ ester (5, zygophyloside B). These five compounds were subjected to the cytotoxicity on MTT assay system. Compound 1 among tested showed the most potent cytotoxicity. Quinovic acid showed less potent cytotoxicity than ursolic acid and sugar linkages to 2 decreased the cytotoxicity. Compound 4 more potent than 3 with indicate that the sulfonyl group significantly enhances the activity. This indicates that the glycosidic linkage in ursane-type triterpenoids has mainly negative effect on cytotoxicity unlike in oleanane-type glycosides.

• Natural Product Sciences
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• v.14 no.1
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• pp.37-46
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• 2008

From the 70% EtOH extract of the roots of Astragalus membranaceus (Leguminosae), fifteen saponins were isolated and identified as astragaloside I (1), isoastragaloside II (2), astragaloside II (3), agroastragaloside I (4), cyclogaleginoside B (5), cycloaraloside A (6), brachyoside B (7), agroastragaloside II (8), astragaloside III (9), astragaloside IV (10), astramembranoside A (11), astramembranoside B (12), cylocanthoside E (13), cyclounifolioside B (14) and azukisaponin V methyl ester (15) by spectroscopic methods. Ten compounds 1 - 3, 5 - 7, 9 - 11 and 14 have cycloastragenol as an aglycon, and four compounds 4, 8 , 12, and 13 have cyclocanthogenin as an aglycon. The hairy roots of A. membranaceus were shown to produce previously unreported cycloartane-type saponins such as agroastragalosides I (4) and II (8) and cycloastragenol $3-O-{\beta}-D-xyloside$ (5), together with the known saponins. This is the first report of these saponins (4, 5, and 8) from the intact plant. Although the occurrence of the oleanane-type triterpene saponin, azukisaponin V methyl ester (15), in Astragalus plants has been demonstrated by others, this is the first report of the azukisaponin V methyl ester (15) from the Astragalus plants.

• Archives of Pharmacal Research
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• v.27 no.12
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• pp.1270-1274
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• 2004

Random amplified polymorphic DNA (RAPD) analysis was used to determine the genetic relationships among seventeen species of the Acanthopanax species. The DNA isolated from the leaves of the samples was used as template in polymerase chain reaction (PCR) with twenty random decamer primers in order to distinguish plant subspecies at the level of their genomes. The RAPD patterns were compared by calculating pairwise distances using Dice similarity index, and produced to the genetic similarity dendrogram by unweighted pair-group method arithmetic averaged (UPGMA) analysis, showing three groups; a major cluster(twelve species), minor cluster (4 species) and single-clustering species. The results of RAPD were compatible with the morphological classification, as well as the chemotaxonomic classification of the Acanthopanax species. The Acanthopanax species containing 3,4-seco-lupane type triterpene compounds in their leaves corresponded to the major cluster, another species having oleanane or normal lupane type constituents to minor clusters, and one species not containing triterpenoidal compound to single-cluster.

• Natural Product Sciences
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• v.14 no.4
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• pp.249-253
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• 2008

Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

• Journal of Pharmacopuncture
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• v.22 no.2
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• pp.55-67
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• 2019

The incidences of cancer are continuously increasing worldwide, affecting life of millions of people. Several factors associated with the internal and external environment are responsible for this deadly disease. The key internal determinants like abnormal hormonal regulation, genetic mutations and external determinants such as lifestyle and occupational factors enhances onset of cancer. From the ancient time, plants were remained as the most trusted source of medicine for the treatment of diverse disease conditions. Extensive studies have been performed for the discovery of effective anticancer agent from the plant and still it is going on. Pentacyclic triterpenoids are biologically active phytochemicals having a different range of activities such as anti-inflammatory, hepatoprotective, anti-hypertensive, antiulcerogenic and anti-tumor. These compounds generally contain ursane, oleanane, lupane and friedelane as a chief skeleton of pentacyclic triterpenoids which are generally present in higher plants. Isoprene unit, phytochemical, with good antitumor/anticancer activity is required for the biosynthesis of pentacyclic triterpenoids. Mechanisms such as cytotoxicity, DNA polymerase inhibition, regulation of apoptosis, change in signal transductions, interfere with angiogenesis and dedifferentiation, antiproliferative activity and metastasis inhibition are might be responsible for their anticancer effect. Present review spotlights diverse targets, mechanisms and pathways of pentacyclic triterpenoids responsible for anticancer effect.

• KOREAN JOURNAL OF CROP SCIENCE
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• v.41 no.spc1
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• pp.145-165
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• 1996

Amaranth(Amaranthus spp. L.) and quinoa (Chenpodium quinoa Willd.) are old crops from South, Central America and Central Asia and their grains have been identified as very promising food crops because of their exceptional nutritive value. Squalene is an important ingredient in skin cosmetics and computer disc lubricants as well as bioactive materials such as inhibition of fungal and mammalian sterol biosynthesis, antitumor, anticancer, and immunomodulation. Amaranth has a component called squalene (2,6,10,15,19,23-hexamethyl-2,6,10,14,22-tetraco-sahexaene) about 1/300 of the seed and $5\~8\%$ of its seed oil. Oil and squalene content in amaranth seed were different for the species investigated. Squalene content in seed oil also increased by $15.5\%$ due to puffing and from 6.96 to $8.01\%$ by refining and bleaching. Saponin concentrations in quinoa seed ranged 0.01 to $5.6\%$. Saponins are located in the outer layers of quinoa grain. These layers include the perianth, pericarp, a seed coat layer, and a cuticle like structure. Oleanane-type triterpenes saponins are of great interest because of their diverse pharmacological properties, for instance, anti-inflammatory, antibiotic, contraceptive, and cholesterol-lowering effects. It is known that quinoa contains a number of structurally diverse saponins including the aglycones, oleanolic acid, hederagenin, and phytolaccagenic acid, which are new potential in gredient for pharmacological properties. It is likely that these saponin levels will be considerably affected by genetic, agronomic and environmental factors as well as by processing. With the current enhanced public interest in health and nutrition amaranth and quinoa will most likely remain in the immediate future within the realm of exotic health foods until such time as agricultural production meets the quantities and qualify required by industrial food manufacturers.

• Natural Product Sciences
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• v.25 no.4
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• pp.317-325
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• 2019

Here, we designed to examine the anti-inflammatory effects on RAW264.7 cells and the immunosuppressive effects by evaluating interleukin-2 (IL-2) production in Jurkat T cells using a MeOH extract of Panax notoginseng roots. The results showed that the MeOH extract inhibited the synthesis of nitric oxide (NO) in a dose-dependent manner (IC₅₀ value of 7.08 ㎍/mL) and displayed effects on T cell activation at a concentration of 400 ㎍/mL. In efforts to identify the potent compounds, bioactivity-guided fractionation of the MeOH extract and chemical investigation of its active CH₂Cl₂-, EtOAc-, and butanol-soluble fractions led to the successful isolation and identification of eleven compounds, including two polyacetylenes (1, 2), a steroid saponin (3), seven dammarane-type ginsenosides (4 - 10), and an oleanane-type ginsenoside (11). Among them, compound 11 was isolated from this plant for the first time. Compound 2 exhibited potent inhibitory effects on NO synthesis and an immunosuppressive effect with IC₅₀ values of 2.28 and 65.57 μM, respectively.